Process of preparing 2-methylselenazoline



Patented May 8, 1934 UNETED STATES PATENT OFFICE PROCESS OF PREPARING Z-METHYL- SELENAZOLINE Frank L. White, Rochester, N. Y., assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New York No Drawing. Original application September 21,

1931, Serial No. 564,138. Divided and this application October 6, 1932, Serial No. 636,529

4 Claims.

' acting a bromoethylamine hydrobromide with As an example of the manner of carrying out my invention, the following preparation of 2- methylselenazoline is illustrative:

10.8 g. (1 mol.) of c-bromoethylamine hydrobromide are heated in a small round-bottomed flask on a steam bath. To this hot fl-bromoethylamine hydrobromide there is added in small portions, over a period of about three minutes while it is stirred with a glass rod 6.5 g. (1 mol.) of freshly prepared selenoacetamide. A melt is formed before all the selenoacetamide is added. The heating is continued for about five minutes, during which time the reaction mixture sets solid in the flask; this solid is dissolved in 200 cc. water, made alkaline by the addition of sodium hydroxide and the Z-methylselenazoline thus liberated distilled from this alkaline solution by steam distillation. About cc. distillate is collected. Some of the Z-methylselenazoline separates as an oil and remains as the bottom layer.

This layer is separated by means of a separatory funnel. The aqueous layer is then treated with pulverized potassium hydroxide whereupon more 2-methylselenazoline separates out, which is collected by extraction with ethyl ether.

ether extract is a This ethyl doled to the 2-methy1selenazoline which has previously been removed from the distillate at the se paratory funnel and the whole is then dried with solid potassium carbonate. After decanting the anhydrous ethyl ether layer (containing the Z-methylselenazoline) from the potassium carbon ate, the ether is distilled off leaving Z-methylselenazoline as a residue which may be further p duced pressure.

urified by distilling under re- The Z-methylselenazoline distills as a colorless liquid boiling at 71-72" C. at 35 mm. pressure of mercury.

What I claim as my invention and desire to secure by Letters Patent of the United States is:

l. Ina process of preparing 2-rnethylselenazoline the step which comprises reacting fl-bromoethylamine hydrcbromide with selenoacetamide under the influence of heat.

2. The process of preparing Z-methylselenazoline which comprises reacting c-bromoethylamine hydrobromide with selenoacetamide under the influence of heat and then liberating Z-rnethylselenazoline from the reaction mass by dissolving the mass in an aqueous solution of an alkali.

3. The process of preparing Z-methylselenazoline which comprises reacting ,B-bromoethylamine hydrobromide with selenoacetamide under the influence of heat and then liberating the 2- methylselenazoline from the reaction mass by dissolving the mass in an aqueous solution of sodium hydroxide.

line.

FRANK L. WHITE. 

